N-Hydroxyphthalimide → 1-acetylamino-3-adamantanol

HRID 1937240

Reaktionsgleichung

Reaktionsgleichung von HRID 1937240
[C:1]([NH:4][C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[CH2:6]1)[CH2:12]2)(=[O:3])[CH3:2].[OH:15]N1C(=O)C2=CC=CC=C2C1=O>C(O)(=O)C>[C:1]([NH:4][C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][C:7]([OH:15])([CH2:8]3)[CH2:6]1)[CH2:12]2)(=[O:3])[CH3:2].[C:1]([NH:4][C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([C:8]3=[O:15])[CH2:6]1)[CH2:12]2)(=[O:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 10665N-HydroxyphthalimideHCID 641531-Acetamidoadamantane

Produkt 2

HCID 28427921-acetylamino-3-adamantanolHCID 5338964N-(4-oxo-1-adamantyl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Mixture of 10 mmole 1-acetylaminoadamantane (Aldrich chemical Company, Inc.), 1 mmole of N-hydroxyphthalimide (NHPI), 0.05 mmole of vanadium(III)acetylacetonato (V(AA)3) and 25 mL of acetic acid was stirred under an oxygen atmosphere and the conditions represented in Table 1 (temperature and time). The products in the reaction mixture were analyzed by gas chromatography, and, as a result, 1-acetylamino-3-adamantanol (compound 1), 1-acetylamino-3,5-adamatanediol (compound 2) and 1-acetylamino-4-adamantanone (compound 3) were obtained with conversions and yields represented in Table 1.

Quellen und Nachweise

ORD-Eintrag
ord-82da175110b64bb58e630e4797e4cdaa
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06392104B1

Verknüpfte Notizen

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